(+)-(4S)-3-<(2'R)-2'-(hydroxymethyl)butanoyl>-4-benzyl-2-oxazolidinone

Base Information

• Chemical Name: (+)-(4S)-3-<(2'R)-2'-(hydroxymethyl)butanoyl>-4-benzyl-2-oxazolidinone
• CAS No.: 150615-45-5
• Molecular Formula: C₁₅H₁₉NO₄
• Molecular Weight: 277.32
• Mol file: 150615-45-5.mol

Synonyms:(+)-(4S)-3-<(2'R)-2'-(hydroxymethyl)butanoyl>-4-benzyl-2-oxazolidinone

Chemical Property of (+)-(4S)-3-<(2'R)-2'-(hydroxymethyl)butanoyl>-4-benzyl-2-oxazolidinone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+)-(4S)-3-<(2'R)-2'-(hydroxymethyl)butanoyl>-4-benzyl-2-oxazolidinone

There total 4 articles about (+)-(4S)-3-<(2'R)-2'-(hydroxymethyl)butanoyl>-4-benzyl-2-oxazolidinone which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

(+)-(4S)-3-<(2'R)-2'-((benzyloxy)methyl)butanoyl>-4-benzyl-2-oxazolidinone (163457-34-9) → (+)-(4S)-3-<(2'R)-2'-(hydroxymethyl)butanoyl>-4-benzyl-2-oxazolidinone (150615-45-5)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethanol; for 72h; Ambient temperature;

DOI:10.1021/jo951653e

Reference yield: 93.0%

Benzyloxymethyl chloride (3587-60-8) + (S)-4-benzyl-3-butyryloxazolidin-2-one (111292-87-6,143097-11-4,112459-79-7) → (+)-(4S)-3-<(2'R)-2'-(hydroxymethyl)butanoyl>-4-benzyl-2-oxazolidinone (150615-45-5)

Guidance literature:

Benzyloxymethyl chloride; (S)-4-benzyl-3-butyryloxazolidin-2-one; With titanium tetrachloride; triethylamine; In dichloromethane; at 0 ℃; for 3h; Inert atmosphere;

With palladium 10% on activated carbon; hydrogen; In ethanol; dichloromethane; at 20 ℃; for 23h; Inert atmosphere;

DOI:10.1016/j.tetlet.2009.02.101

Reference yield:

(S)-4-benzyl-3-butyryloxazolidin-2-one (111292-87-6,143097-11-4,112459-79-7) → (+)-(4S)-3-<(2'R)-2'-(hydroxymethyl)butanoyl>-4-benzyl-2-oxazolidinone (150615-45-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 78 percent / TiCl₄; NEt₃

2: 100 percent / H₂ / Pd/C

With hydrogen; titanium tetrachloride; triethylamine; palladium on activated charcoal; 1: Evans alkylation;

DOI:10.1021/ja025606x

upstream raw materials:

1,3,5-Trioxan

(S)-4-benzyl-3-butyryloxazolidin-2-one

(+)-(4S)-3-<(2'R)-2'-((benzyloxy)methyl)butanoyl>-4-benzyl-2-oxazolidinone

Benzyloxymethyl chloride

Downstream raw materials:

(+)-(4S)-3-<(2'R)-2'-((tert-Butyldimethylsiloxy)methyl)butanoyl>-4-benzyl-2-oxazolidinone

(-)-p-fluorophenyl (2E)-4-<((2'R)-2'-((tert-butyldimethylsiloxy)methyl)butanoyl)oxy>-2-butenoate

(E)-4-((R)-2-Hydroxymethyl-butyryloxy)-but-2-enoic acid 4-fluoro-phenyl ester

(-)-p-fluorophenyl (2E)-4-<((2'R)-2'-(bromomethyl)butanoyl)oxy>-2-butenoate